Ronnie Milsap was one of my first 10 or 20 CW contacts as a new novice in the 70's. Didn't know his last name till I looked his call up in the Call Book. Remember that monster?
Barry Goldwater was a regular on the 07/67 machine in Baltimore. He would hit it when he was flying in and out of DC, liked the coverage of that repeater.
My favorite qso happened after I finished running phone patches on 15 mtrs to Mcmurdo AFB at abt 3 or 4 AM back in the early 80's when I got a call from JY1. No suffix and thought he was a pirate station but decided to work him. In the qso he asked me what I did for work and I told him that I managed a Radio Shack. He told me he had one of everything they ever sold and I said to myself "Shuuuuuure"
Then I asked him what his line of work was and that's when I made the mistake of addressing him as Your Highness. I received a lecture that there are no titles or royalties in ham radio, only first names. It was a nice chewing out and I remember he had a good sense of humor.